I use the bi-annual Ubuntu Long-Term Support (LTS) for my web hosts, but I stay at least a year old for new sites, and at least two years old for old ones. I consider rock-solid stability to be more important than new features. An Ubuntu release comes out in April, and is numbered with the year before the decimal point and the month (April = 4) after the decimal point. Even years are LTS releases. Odd years are not. So the most recent LTS was Ubuntu 20.04. An LTS is supported for 5 years, meaning that in April of 2021, the 16.04 release will stop being supported. This web server is currently running on Ubuntu 16.04, so it's time to upgrade to 18.04.
Upgrades usually work fine, but not always, and they take a while, so I'm going to do it as follows:
1. Bring the machine down, and create a snapshot. This usually takes 10 minutes or so.
2. Bring the machine back up.
3. Create a new droplet (virtual machine) from the snapshot.
4. Install the phpzip extension, which Cindy needs for one of Elias's web sites.
5. Upgrade to Ubuntu 18.04
6. Disable the web server on the live site.
7. Back up databases and uploads.
8. Restore the databases and uploads into the new droplet.
9. Change the DNS to point to the new droplet.
After things appear to be working for a few days, I'll delete the old droplet. It will cost a few dollars to have multiple droplets for a few days, but the warm fuzzy feeling will be worth it (to me).
I will probably do steps 1 and 2 on Friday night, and hope to finish step 9 by the end of the weekend.